Tipu I don’t think you are worrying too much. These are all valid concerns and anyone giving their sis/daughter to someone like that should have these concerns. I would have the same concerns if I were in your place. What you have to look for is if the guy is ambitious and otherwise covers all the bases and is indeed a nice decent guy. You might want to ask him why did he not finish a degree. Degree/ education is something that he can attain at any point in time. Maybe you would want to ask him if he would be up for perusing a better education. Lastly, just because he spends alot on this family that doesn’t not necessarily translate into a bad thing. It only means he cares a lot about his family and probably (not for certain) will care in the same way about anyone else who joins his family.